For your original characters or your fictional favorites!
1. Everyday/casual/what they wear the most
2. Formal/black tie
3. Swimwear (ALT: on vacation)
4. Underwear (ALT: in a Snuggie or sweats)
5. Sportswear/exercise gear (ALT: trying to look tough)
6. Pajamas/sleepwear
7. At work/school (ALT: forced to attend a boring semi-formal event—graduation, family reunion, religious service, wedding, etc.)
8. Spring
9. Autumn
10. In very cold weather
11. In very hot weather
12. Rainy day (outdoors or indoors, your call)
13. Having a relaxing, lazy Sunday at home
14. Out in public but too tired to even try (or otherwise disheveled)
15. What they wear when they’re feeling confident/want to feel confident
16. On a date (ALT: at a restaurant/diner or enjoying a nice solitary walk/bike ride)
17. At a party or club (ALT: street fashion)
18. A favorite/prized item or outfit that they might reserve for certain occasions
19. What they wore as a kid/teenager (ALT: an item or outfit they love that everyone else thinks is ugly/unflattering)
20. In something another character made them wear (ALT: a personal item they are embarrassed to love)
21. Something from your wardrobe that they’d be most likely to wear (ALT: in something they would never wear in a million years and totally rocking it)
22. Something (esp. out of character) that would make you laugh if you saw them wear it—e.g. a zazzle-poetry shirt, something you saw on TV, rollerskates, etc.
23. Incognito
24. Ugly sweater/thrift/vintage
25. Costume/cosplay (ALT: what they’d wear in a fictional universe of your choosing—e.g. in Middle Earth, as a Crystal Gem, as a Pokémon trainer, aboard Serenity, etc.)
26. Retro/period costume (ALT: the future or, if applicable, what they’d look like in contemporary society/our universe)
27. Subculture of your choice
28. In a ridiculously luxurious/regal ensemble (if they already dress ostentatiously, give them a makeunder)
29. Palette swap! Use a color scheme they wouldn’t normally wear—e.g. pastels if they usually wear all black, neons if they’re otherwise into neutrals
30. Any of the alternative prompts you’d like to try (ALT: WILD CARD!!)
I neglected to mention this in the original post, but if you don’t feel comfortable drawing, you can use Polyvore or something similar if you want! You can even do both—I’m not gonna stop you.